James Robertson was born in 1742 in Brunswick County, Virginia, and moved to North Carolina when he was a child. Following his marriage to Charlotte Reeves, he and his wife migrated across the Appalachian Mountains and settled on the Watauga River, in what would become upper East Tennessee. Robertson became noted for the strength of his character and for his skills as a soldier, and when new settlements were planned far to the west in the Cumberland wilderness, he was selected to be a leader.

In early 1779 James Robertson took a few men west to explore and make preparations at the French Lick, close to where the new settlements would be located. He returned home and that fall he came west a second time, bringing his livestock and leading another small group to the settlements. Within a few months the inhabitants were under constant Indian attack, and while the vast majority fled, Robertson refused to leave the wilderness colony.

James Robertson not only made journeys back across the mountains to obtain support for the struggling settlements, he repeatedly used his powers of persuasion to keep the settlers from abandoning their homes, and he also maintained a difficult and crucial alliance with the Chickasaw nation. Warfare plagued the Cumberland frontier for fifteen years, and during the period when he was providing such outstanding leadership, two of his sons were killed by Indians and he was wounded three times. Robertson continued his leadership after peace was established, and when he died in 1814 he was serving as the American agent to the Chickasaws. James Robertson was among the greatest leaders America ever produced. Without his tenacious leadership, the Cumberland settlements would not have survived, and had they not survived, the history of the nation would have followed a far different course.